4-hydroxy-6-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3-phenylthiomethyl-2H-pyran-2-one

Base Information

Chemical Name:4-hydroxy-6-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3-phenylthiomethyl-2H-pyran-2-one
CAS No.:327162-11-8
Molecular Formula:C₂₃H₂₆O₃S
Molecular Weight:382.524
Hs Code.:

Synonyms:4-hydroxy-6-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3-phenylthiomethyl-2H-pyran-2-one

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Chemical Property of 4-hydroxy-6-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3-phenylthiomethyl-2H-pyran-2-one

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Technology Process of 4-hydroxy-6-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3-phenylthiomethyl-2H-pyran-2-one

There total 17 articles about 4-hydroxy-6-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3-phenylthiomethyl-2H-pyran-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 108-98-5
thiophenol

: 327162-10-7
4-hydroxy-6-[(1R,2R,4aR,8S,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methylnaphthyl]-2H-pyran-2-one

: 327162-11-8
4-hydroxy-6-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3-phenylthiomethyl-2H-pyran-2-one

Guidance literature:: With piperidine; acetic acid; In ethanol;
DOI:10.1021/ol006893h

Reference yield:

: 327162-06-1
(1R,2R,4aS,8aR)-(2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methanol

: 327162-11-8
4-hydroxy-6-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3-phenylthiomethyl-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 17 mg / pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

2.1: titanium(IV) chloride / CH₂Cl₂ / -78 °C

2.2: 20 mg / Jones reagent / acetone / 0 °C

3.1: 93 percent / 1,8-diazobicyclo[5.4.0]undec-7-ene / benzene / 2.5 h / 60 °C

4.1: 82 percent / acetic acid; piperidine / ethanol / 17 h / 55 °C

With piperidine; 4 A molecular sieve; titanium tetrachloride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In ethanol; dichloromethane; benzene; 2.2: Jones oxidation;
DOI:10.1021/jo0163602

Reference yield:

: 178241-41-3
O-[(1S,2R,4aR,8S,8aR)-methyl-1,2,3,4a,6,7,8,8a-octahydro-8-hydroxy-2-methylnaphthalen-4(5H)-one-1-carboxylate-8-yl]thiocarboxyimidazolide

: 327162-11-8
4-hydroxy-6-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3-phenylthiomethyl-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: 93 percent / azobisisobutyronitrile; n-tributyltinhydride / benzene / 1 h / 60 °C

2.1: 90 percent / L-selectride; sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 11.5 h / 20 °C

3.1: 78 percent / potassium tert-butoxide / dimethylsulfoxide; 2-methyl-propan-2-ol / 23 h / 20 °C

4.1: potassium tert-butoxide / tetrahydrofuran / 0.83 h / -35 °C

5.1: 258.1 mg / tetrahydrofuran / 0.17 h

6.1: 1-methylnaphthalene / 3 h / 190 °C

7.1: 22 mg / lithium aluminium hydride / diethyl ether / 0.25 h / 0 °C

8.1: 17 mg / pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

9.1: titanium(IV) chloride / CH₂Cl₂ / -78 °C

9.2: 20 mg / Jones reagent / acetone / 0 °C

10.1: 93 percent / 1,8-diazobicyclo[5.4.0]undec-7-ene / benzene / 2.5 h / 60 °C

11.1: 82 percent / acetic acid; piperidine / ethanol / 17 h / 55 °C

With piperidine; sodium hydroxide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; potassium tert-butylate; dihydrogen peroxide; tri-n-butyl-tin hydride; titanium tetrachloride; L-Selectride; acetic acid; 1-Methylnaphthalene; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; benzene; 9.2: Jones oxidation;
DOI:10.1021/jo0163602